(E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinol-yl)-3-(4-ethoxy-phen-yl)prop-2-en-1-one.

In the title compound, C(27)H(22)ClNO(2), the phenyl substituent on the quinoline ring system is almost perpendicular to it [dihedral angle = 88.2 (1)°]. The quinoline ring system and the ethoxy-phenyl ring are oriented at dihedral angles of 79.5 (1) and 17.6 (3)°, respectively, with respect to the almost planar [r.m.s. deviation= 0.037 (3) Å] -C(=O)-C=C- linkage. In the crystal, the inversion-related mol-ecules exist as C-H⋯O hydrogen-bonded R(2) (2)(8) dimers.

Related literature

For the biological activity of chalcone derivatives, see: Dimmock et al. (1999 ▶); Zi & Simoneau (2005 ▶); Yamazaki et al. (2002 ▶). For a related structure, see: Wu et al. (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C27H22ClNO2

M = 427.91

Monoclinic,

a = 16.2086 (5) Å

b = 13.4760 (4) Å

c = 10.5450 (3) Å

β = 105.128 (2)°

V = 2223.49 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.52 × 0.14 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.905, T max = 0.986

39732 measured reflections

6511 independent reflections

2360 reflections with I > 2σ(I)

R int = 0.110

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.169

S = 1.00

6511 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001248/ci5014sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001248/ci5014Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H22ClNO2	F(000) = 896
Mr = 427.91	Dx = 1.278 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2856 reflections
a = 16.2086 (5) Å	θ = 2.5–19.7°
b = 13.4760 (4) Å	µ = 0.20 mm−1
c = 10.5450 (3) Å	T = 296 K
β = 105.128 (2)°	Plate, colourless
V = 2223.49 (11) Å3	0.52 × 0.14 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6511 independent reflections
Radiation source: fine-focus sealed tube	2360 reflections with I > 2σ(I)
graphite	Rint = 0.110
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
Tmin = 0.905, Tmax = 0.986	k = −18→19
39732 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0605P)2] where P = (Fo2 + 2Fc2)/3
6511 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	1.16190 (5)	0.67801 (6)	0.88581 (7)	0.0828 (3)
O1	0.64844 (13)	0.61168 (16)	0.6171 (2)	0.0913 (7)
O2	0.56628 (11)	−0.02725 (14)	0.68435 (17)	0.0742 (5)
N1	0.83573 (15)	0.60187 (15)	1.01410 (19)	0.0652 (6)
C1	0.76675 (18)	0.57733 (18)	0.9210 (3)	0.0636 (7)
C2	0.91019 (17)	0.61647 (17)	0.9804 (2)	0.0561 (6)
C3	0.98340 (19)	0.64653 (18)	1.0782 (2)	0.0681 (8)
H3A	0.9796	0.6536	1.1643	0.082*
C4	1.05818 (18)	0.66517 (19)	1.0508 (2)	0.0669 (8)
H4A	1.1052	0.6855	1.1169	0.080*
C5	1.06500 (16)	0.65382 (17)	0.9211 (2)	0.0598 (7)
C6	0.99656 (16)	0.62385 (17)	0.8232 (2)	0.0571 (7)
H6A	1.0023	0.6157	0.7383	0.068*
C7	0.91777 (16)	0.60528 (16)	0.8499 (2)	0.0516 (6)
C8	0.84261 (17)	0.57688 (16)	0.7512 (2)	0.0533 (6)
C9	0.76818 (16)	0.56417 (18)	0.7873 (2)	0.0568 (6)
C10	0.84861 (15)	0.56255 (19)	0.6129 (2)	0.0535 (6)
C11	0.83198 (18)	0.6399 (2)	0.5248 (3)	0.0722 (8)
H11A	0.8149	0.7011	0.5499	0.087*
C12	0.8408 (2)	0.6264 (3)	0.3979 (3)	0.0832 (9)
H12A	0.8296	0.6789	0.3386	0.100*
C13	0.86553 (19)	0.5372 (3)	0.3599 (3)	0.0793 (9)
H13A	0.8711	0.5287	0.2751	0.095*
C14	0.88206 (19)	0.4605 (2)	0.4470 (3)	0.0809 (9)
H14A	0.8990	0.3994	0.4213	0.097*
C15	0.87381 (17)	0.4728 (2)	0.5731 (2)	0.0696 (8)
H15A	0.8854	0.4200	0.6318	0.084*
C16	0.68610 (18)	0.5431 (2)	0.6824 (3)	0.0674 (7)
C17	0.65339 (17)	0.4419 (2)	0.6605 (3)	0.0714 (8)
H17A	0.6050	0.4311	0.5917	0.086*
C18	0.68782 (17)	0.3647 (2)	0.7317 (3)	0.0701 (8)
H18A	0.7369	0.3770	0.7985	0.084*
C19	0.65760 (16)	0.2617 (2)	0.7177 (3)	0.0647 (7)
C20	0.59824 (17)	0.2271 (2)	0.6052 (2)	0.0719 (8)
H20A	0.5783	0.2696	0.5344	0.086*
C21	0.56885 (17)	0.1309 (2)	0.5978 (3)	0.0703 (8)
H21A	0.5291	0.1092	0.5224	0.084*
C22	0.59809 (16)	0.0660 (2)	0.7018 (2)	0.0630 (7)
C23	0.65787 (18)	0.0995 (2)	0.8127 (3)	0.0750 (8)
H23A	0.6782	0.0570	0.8835	0.090*
C24	0.68682 (17)	0.1947 (2)	0.8180 (3)	0.0747 (8)
H24A	0.7280	0.2153	0.8923	0.090*
C25	0.68576 (19)	0.5650 (2)	0.9637 (3)	0.0906 (10)
H25A	0.6887	0.6049	1.0401	0.136*
H25B	0.6790	0.4965	0.9842	0.136*
H25C	0.6379	0.5855	0.8940	0.136*
C26	0.5940 (2)	−0.0967 (2)	0.7886 (3)	0.0938 (10)
H26A	0.5725	−0.0777	0.8627	0.113*
H26B	0.6560	−0.0977	0.8171	0.113*
C27	0.5619 (2)	−0.1949 (3)	0.7416 (4)	0.1204 (13)
H27A	0.5787	−0.2420	0.8119	0.181*
H27B	0.5853	−0.2142	0.6705	0.181*
H27C	0.5007	−0.1930	0.7115	0.181*

	U11	U22	U33	U12	U13	U23
Cl1	0.0758 (5)	0.1044 (6)	0.0655 (5)	−0.0208 (4)	0.0137 (4)	−0.0139 (4)
O1	0.0965 (16)	0.0922 (16)	0.0772 (14)	0.0004 (12)	0.0081 (12)	0.0054 (12)
O2	0.0882 (13)	0.0688 (13)	0.0590 (11)	−0.0121 (10)	0.0075 (10)	0.0023 (10)
N1	0.0898 (17)	0.0651 (15)	0.0463 (12)	−0.0059 (12)	0.0280 (12)	−0.0022 (11)
C1	0.0804 (19)	0.0612 (18)	0.0541 (16)	−0.0052 (14)	0.0260 (15)	−0.0026 (13)
C2	0.0806 (18)	0.0504 (15)	0.0389 (13)	−0.0023 (13)	0.0184 (13)	−0.0007 (11)
C3	0.094 (2)	0.0725 (19)	0.0371 (14)	−0.0044 (16)	0.0162 (14)	−0.0061 (12)
C4	0.081 (2)	0.0707 (19)	0.0420 (15)	−0.0070 (15)	0.0034 (13)	−0.0071 (12)
C5	0.0687 (16)	0.0581 (16)	0.0504 (15)	−0.0073 (13)	0.0117 (13)	−0.0033 (12)
C6	0.0786 (18)	0.0543 (16)	0.0388 (13)	−0.0073 (13)	0.0163 (13)	−0.0064 (11)
C7	0.0695 (17)	0.0473 (14)	0.0390 (13)	−0.0068 (12)	0.0156 (12)	−0.0027 (11)
C8	0.0747 (17)	0.0473 (15)	0.0399 (13)	−0.0062 (12)	0.0183 (12)	−0.0037 (11)
C9	0.0734 (17)	0.0563 (16)	0.0447 (14)	−0.0080 (13)	0.0225 (13)	−0.0049 (12)
C10	0.0654 (15)	0.0565 (16)	0.0392 (13)	−0.0126 (13)	0.0149 (11)	−0.0048 (12)
C11	0.103 (2)	0.0622 (18)	0.0529 (16)	−0.0086 (15)	0.0231 (15)	0.0024 (14)
C12	0.114 (3)	0.087 (2)	0.0502 (17)	−0.0144 (19)	0.0245 (16)	0.0127 (16)
C13	0.098 (2)	0.097 (2)	0.0477 (16)	−0.0237 (19)	0.0279 (15)	−0.0128 (17)
C14	0.110 (2)	0.082 (2)	0.0560 (17)	−0.0013 (18)	0.0304 (16)	−0.0156 (16)
C15	0.098 (2)	0.0667 (19)	0.0445 (15)	0.0004 (16)	0.0189 (14)	−0.0033 (13)
C16	0.0715 (18)	0.079 (2)	0.0556 (17)	−0.0056 (16)	0.0246 (14)	−0.0067 (15)
C17	0.0646 (17)	0.086 (2)	0.0619 (17)	−0.0129 (16)	0.0134 (14)	−0.0095 (16)
C18	0.0642 (17)	0.087 (2)	0.0605 (17)	−0.0086 (16)	0.0194 (14)	−0.0137 (16)
C19	0.0628 (16)	0.074 (2)	0.0585 (17)	−0.0095 (14)	0.0173 (13)	−0.0157 (15)
C20	0.0791 (19)	0.077 (2)	0.0561 (16)	−0.0072 (16)	0.0119 (14)	−0.0001 (14)
C21	0.0769 (18)	0.075 (2)	0.0530 (16)	−0.0084 (15)	0.0059 (14)	−0.0069 (15)
C22	0.0636 (16)	0.073 (2)	0.0526 (16)	−0.0015 (14)	0.0158 (13)	−0.0058 (14)
C23	0.0748 (19)	0.088 (2)	0.0554 (17)	−0.0078 (16)	0.0048 (14)	0.0013 (15)
C24	0.0687 (18)	0.088 (2)	0.0593 (17)	−0.0090 (16)	0.0017 (14)	−0.0070 (17)
C25	0.097 (2)	0.116 (3)	0.0730 (19)	−0.0114 (19)	0.0472 (17)	−0.0061 (18)
C26	0.103 (2)	0.094 (3)	0.073 (2)	−0.0185 (19)	0.0026 (18)	0.0186 (19)
C27	0.141 (3)	0.099 (3)	0.119 (3)	−0.012 (2)	0.029 (2)	0.034 (2)

Cl1—C5	1.737 (3)	C13—H13A	0.93
O1—C16	1.217 (3)	C14—C15	1.382 (3)
O2—C22	1.352 (3)	C14—H14A	0.93
O2—C26	1.424 (3)	C15—H15A	0.93
N1—C1	1.323 (3)	C16—C17	1.460 (4)
N1—C2	1.359 (3)	C17—C18	1.319 (4)
C1—C9	1.427 (3)	C17—H17A	0.93
C1—C25	1.504 (4)	C18—C19	1.467 (4)
C2—C3	1.414 (3)	C18—H18A	0.93
C2—C7	1.421 (3)	C19—C24	1.376 (4)
C3—C4	1.341 (3)	C19—C20	1.398 (3)
C3—H3A	0.93	C20—C21	1.376 (4)
C4—C5	1.408 (3)	C20—H20A	0.93
C4—H4A	0.93	C21—C22	1.386 (3)
C5—C6	1.365 (3)	C21—H21A	0.93
C6—C7	1.400 (3)	C22—C23	1.385 (3)
C6—H6A	0.93	C23—C24	1.362 (4)
C7—C8	1.432 (3)	C23—H23A	0.93
C8—C9	1.367 (3)	C24—H24A	0.93
C8—C10	1.500 (3)	C25—H25A	0.96
C9—C16	1.518 (4)	C25—H25B	0.96
C10—C11	1.375 (3)	C25—H25C	0.96
C10—C15	1.376 (3)	C26—C27	1.460 (4)
C11—C12	1.395 (4)	C26—H26A	0.97
C11—H11A	0.93	C26—H26B	0.97
C12—C13	1.360 (4)	C27—H27A	0.96
C12—H12A	0.93	C27—H27B	0.96
C13—C14	1.362 (4)	C27—H27C	0.96
C22—O2—C26	118.2 (2)	C14—C15—H15A	119.7
C1—N1—C2	118.6 (2)	O1—C16—C17	120.8 (3)
N1—C1—C9	122.4 (2)	O1—C16—C9	119.0 (3)
N1—C1—C25	116.1 (2)	C17—C16—C9	120.2 (3)
C9—C1—C25	121.5 (2)	C18—C17—C16	124.4 (3)
N1—C2—C3	119.0 (2)	C18—C17—H17A	117.8
N1—C2—C7	123.1 (2)	C16—C17—H17A	117.8
C3—C2—C7	118.0 (3)	C17—C18—C19	127.5 (3)
C4—C3—C2	122.0 (2)	C17—C18—H18A	116.2
C4—C3—H3A	119.0	C19—C18—H18A	116.2
C2—C3—H3A	119.0	C24—C19—C20	117.1 (3)
C3—C4—C5	119.6 (2)	C24—C19—C18	120.3 (2)
C3—C4—H4A	120.2	C20—C19—C18	122.6 (3)
C5—C4—H4A	120.2	C21—C20—C19	120.9 (3)
C6—C5—C4	120.8 (3)	C21—C20—H20A	119.6
C6—C5—Cl1	119.7 (2)	C19—C20—H20A	119.6
C4—C5—Cl1	119.5 (2)	C20—C21—C22	120.5 (2)
C5—C6—C7	120.3 (2)	C20—C21—H21A	119.7
C5—C6—H6A	119.8	C22—C21—H21A	119.7
C7—C6—H6A	119.8	O2—C22—C23	125.1 (3)
C6—C7—C2	119.3 (2)	O2—C22—C21	116.0 (2)
C6—C7—C8	123.3 (2)	C23—C22—C21	118.8 (3)
C2—C7—C8	117.4 (2)	C24—C23—C22	119.9 (3)
C9—C8—C7	118.5 (2)	C24—C23—H23A	120.0
C9—C8—C10	122.7 (2)	C22—C23—H23A	120.0
C7—C8—C10	118.8 (2)	C23—C24—C19	122.7 (2)
C8—C9—C1	120.1 (2)	C23—C24—H24A	118.6
C8—C9—C16	119.3 (2)	C19—C24—H24A	118.6
C1—C9—C16	120.4 (2)	C1—C25—H25A	109.5
C11—C10—C15	118.8 (2)	C1—C25—H25B	109.5
C11—C10—C8	120.5 (2)	H25A—C25—H25B	109.5
C15—C10—C8	120.6 (2)	C1—C25—H25C	109.5
C10—C11—C12	119.9 (3)	H25A—C25—H25C	109.5
C10—C11—H11A	120.1	H25B—C25—H25C	109.5
C12—C11—H11A	120.1	O2—C26—C27	108.7 (2)
C13—C12—C11	120.6 (3)	O2—C26—H26A	109.9
C13—C12—H12A	119.7	C27—C26—H26A	109.9
C11—C12—H12A	119.7	O2—C26—H26B	109.9
C12—C13—C14	119.6 (3)	C27—C26—H26B	109.9
C12—C13—H13A	120.2	H26A—C26—H26B	108.3
C14—C13—H13A	120.2	C26—C27—H27A	109.5
C13—C14—C15	120.4 (3)	C26—C27—H27B	109.5
C13—C14—H14A	119.8	H27A—C27—H27B	109.5
C15—C14—H14A	119.8	C26—C27—H27C	109.5
C10—C15—C14	120.7 (3)	H27A—C27—H27C	109.5
C10—C15—H15A	119.7	H27B—C27—H27C	109.5
C2—N1—C1—C9	1.0 (4)	C7—C8—C10—C15	86.0 (3)
C2—N1—C1—C25	−178.4 (2)	C15—C10—C11—C12	0.0 (4)
C1—N1—C2—C3	177.5 (2)	C8—C10—C11—C12	177.7 (3)
C1—N1—C2—C7	−0.9 (4)	C10—C11—C12—C13	0.2 (4)
N1—C2—C3—C4	−177.9 (2)	C11—C12—C13—C14	−0.2 (5)
C7—C2—C3—C4	0.6 (4)	C12—C13—C14—C15	0.0 (5)
C2—C3—C4—C5	−0.6 (4)	C11—C10—C15—C14	−0.2 (4)
C3—C4—C5—C6	−0.2 (4)	C8—C10—C15—C14	−177.9 (3)
C3—C4—C5—Cl1	180.0 (2)	C13—C14—C15—C10	0.2 (4)
C4—C5—C6—C7	1.0 (4)	C8—C9—C16—O1	−79.3 (3)
Cl1—C5—C6—C7	−179.20 (18)	C1—C9—C16—O1	96.4 (3)
C5—C6—C7—C2	−1.0 (4)	C8—C9—C16—C17	100.5 (3)
C5—C6—C7—C8	177.8 (2)	C1—C9—C16—C17	−83.8 (3)
N1—C2—C7—C6	178.6 (2)	O1—C16—C17—C18	−176.1 (3)
C3—C2—C7—C6	0.2 (3)	C9—C16—C17—C18	4.1 (4)
N1—C2—C7—C8	−0.3 (3)	C16—C17—C18—C19	178.4 (2)
C3—C2—C7—C8	−178.7 (2)	C17—C18—C19—C24	−163.6 (3)
C6—C7—C8—C9	−177.6 (2)	C17—C18—C19—C20	15.7 (4)
C2—C7—C8—C9	1.3 (3)	C24—C19—C20—C21	1.9 (4)
C6—C7—C8—C10	2.3 (3)	C18—C19—C20—C21	−177.4 (3)
C2—C7—C8—C10	−178.9 (2)	C19—C20—C21—C22	−0.4 (4)
C7—C8—C9—C1	−1.2 (3)	C26—O2—C22—C23	1.8 (4)
C10—C8—C9—C1	179.0 (2)	C26—O2—C22—C21	−179.7 (3)
C7—C8—C9—C16	174.6 (2)	C20—C21—C22—O2	−179.1 (3)
C10—C8—C9—C16	−5.2 (4)	C20—C21—C22—C23	−0.5 (4)
N1—C1—C9—C8	0.0 (4)	O2—C22—C23—C24	178.4 (3)
C25—C1—C9—C8	179.4 (2)	C21—C22—C23—C24	0.0 (4)
N1—C1—C9—C16	−175.7 (2)	C22—C23—C24—C19	1.6 (4)
C25—C1—C9—C16	3.7 (4)	C20—C19—C24—C23	−2.5 (4)
C9—C8—C10—C11	88.1 (3)	C18—C19—C24—C23	176.8 (3)
C7—C8—C10—C11	−91.7 (3)	C22—O2—C26—C27	−171.7 (3)
C9—C8—C10—C15	−94.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···O2i	0.93	2.57	3.493 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21A⋯O2i	0.93	2.57	3.493 (3)	172

Symmetry code: (i) .